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WO2017111439A1 - Composé organique et dispositif électroluminescent organique comprenant ledit composé - Google Patents

Composé organique et dispositif électroluminescent organique comprenant ledit composé Download PDF

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WO2017111439A1
WO2017111439A1 PCT/KR2016/014958 KR2016014958W WO2017111439A1 WO 2017111439 A1 WO2017111439 A1 WO 2017111439A1 KR 2016014958 W KR2016014958 W KR 2016014958W WO 2017111439 A1 WO2017111439 A1 WO 2017111439A1
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aryl
alkyl
boron
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이용환
김영배
김회문
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Doosan Corp
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Definitions

  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB hole blocking layer
  • BCP hole blocking layer
  • electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
  • metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1):
  • At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl groups, C 2 to C 40 alkenyl groups, C 2 to C 40 alkynyl groups, C 6 to C 60 aryl groups, nuclear atoms 5 to 60 heteroaryl groups, C 6 to C 60 aryl jade group, C 1 ⁇ C 40 alkyloxy group of, C 6 ⁇ C 60 aryl amine group
  • the present invention includes an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers provides an organic electroluminescent device comprising the compound of Formula 1. .
  • Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
  • Alkenyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
  • Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
  • the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
  • R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
  • examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
  • Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the compound represented by Formula 1 according to the present invention is excellent in thermal stability, hole transporting, hole injection performance, electron transporting and electron injection performance, and excellent phosphorescence characteristics of the light emitting layer, so that the organic material layer material of the organic electroluminescent device, preferably May be used as the light emitting layer material.
  • the present invention provides a compound represented by Formula 1:
  • At least one of X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , and X 7 and X 8 are each independently represented by the following Chemical Formula 2 or 3 Condensed with a ring to form a condensed ring;
  • X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy of C 60 group, C 1 ⁇ C 40 alkyloxy group of, C 6
  • the novel compound according to the present invention is a structure in which a 5-membered ring is condensed at the terminal of the fluorene moiety to form a basic skeleton, and various substituents are connected to the basic skeleton, specifically represented by the following Chemical Formula 1 do:
  • X 1 to X 8 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • Y 1 to Y 3 are each independently selected from the group consisting of O, S, N (R 4 ) and C (R 5 ) (R 6 );
  • Z 1 and Z 2 are each independently N or C (R 7 );
  • L 1 to L 4 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 1 to R 7 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- aryloxy group of C 60, C 3 ⁇ C 40 alkylsilyl group, C group 6 ⁇ C 60 aryl silyl, C 1 ⁇ arylboronic of C 40 group of an alkyl boron, C 6 ⁇ C 60 group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond
  • Arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy of C 60 time, C 1 ⁇ C 40 alkyloxy group of, C 6
  • the compound represented by Chemical Formula 1 is larger in molecular weight than the conventional organic electroluminescent device material [eg, 4,4-dicarbazolybiphenyl (CBP)], and has a wide energy band gap. While having, it is possible to increase the binding force between the hole and the electron. Therefore, when the compound of Formula 1 is used in an organic electroluminescent device, the driving voltage, efficiency (luminescence efficiency, power efficiency), lifetime, and luminance of the device may be improved.
  • the conventional organic electroluminescent device material eg, 4,4-dicarbazolybiphenyl (CBP)
  • At least one of the Y 1 to Y 3 may include a hetero atom.
  • the ring represented by Formula 2 may be a ring represented by any one of the following formulas 4 to 6:
  • the dotted line means the part where condensation takes place
  • R 5 and R 6 are as defined in formula (I).
  • At least one of the Y 1 , Z 1 and Z 2 may include a hetero atom.
  • the ring represented by Formula 3 may be a ring represented by any one of the following Formula 7 to 12:
  • the dotted line means the part where condensation takes place
  • R 4 and R 7 are the same as defined in Chemical Formula 1. However, in Chemical Formula 9, two R 7 are the same as or different from each other.
  • L 1 to L 4 are each independently composed of a single bond, phenylene group, biphenylene group, pyridinyl group, pyrimidinyl group, naphthalenyl group, fluorenyl group and carbazolyl group Can be selected from the group.
  • R 1 and R 2 are each independently selected from the group consisting of C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms Can be selected.
  • R 1 and R 2 may be independently selected from the group consisting of a methyl group, an ethyl group, a propyl group and substituents represented by the following formulas (13) to (17):
  • T 1 to T 8 are each independently N or C (R 8 );
  • any one of T 1 to T 4 bonded to L 2 or L 4 is C (R 8 ), wherein R 8 is absent;
  • R 8 to R 11 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • the substituent represented by Formula 13 or 14 may be selected from the group consisting of the following Formula F-1 to F-13:
  • t is an integer from 0 to 5;
  • l is an integer from 0 to 4.
  • v is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 12 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ⁇ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylsilyl group, or may be combined with adjacent groups to form a condensed ring, when
  • R 8 is as defined in Formulas 13 and 14 above.
  • each of R 9 to R 11 is independently hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and 5 to 60 heteroaryl group of nuclear atoms It may be selected from the group, more preferably may be selected from the group consisting of phenyl group, biphenyl group, naphthalenyl group, pyridinyl group, pyrimidinyl group, quinolinyl group and quinazolinyl group.
  • L 1 to L 4 is a single bond, R 1 and R 2 may be bonded to form a condensed ring.
  • the compound represented by Formula 1 may be a compound represented by Formula 18:
  • K 1 is selected from the group consisting of a single bond, C (R 13 ) (R 14 ), N (R 15 ), O and S;
  • R 13 to R 15 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ for C 60 aryl phosphazene group, and groups bonded to adjacent or selected from the group consisting of an arylamine C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of which they
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 13 to R 15 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • X 1 to X 8 , and X 9 to X 16 which do not form a condensed ring with a ring represented by the following Chemical Formula 2 or 3 are each independently N or C (R 3 );
  • the dotted line means the part where condensation takes place
  • R 3 Y 1 to Y 3 , Z 1 and Z 2 are as defined in Chemical Formulas 1 to 3 above.
  • At least one of the X 9 And X 10 , X 10 And X 11 , X 11 And X 12 , X 13 And X 14 , X 14 And X 15 , And X 15 And X 16 are each independently condensed with a ring represented by Formula 2 or 3 to form a condensed ring;
  • X 9 to X 16 which do not form a condensed ring with the ring represented by Formula 2 or 3 are each independently N or C (R 3 );
  • R 3 is as defined in Formula 1 above.
  • At least one of the R 3 to R 7 may be each independently a substituent represented by the following formula (19):
  • L 5 and L 6 are selected from the group consisting of a single bond, a C 6 -C 18 arylene group and a heteroarylene group having 5 to 18 nuclear atoms;
  • R 16 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 3 -C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha Condensation in combination with a group selected from or adjacent to (eg, L 5 or other R 3 to R 7 ) a group consisting of a silyl group, a C 6 -C 60 mono or diarylphosphinyl group and a
  • L 5 and L 6 are each a single bond, each independently, a phenylene group, biphenylene group, a pyridinyl group, a pyrimidinyl group, a naphthyl Frontale group, a fluorenyl group, a carbazolyl group, It may be selected from the group consisting of a quinolinyl group and a quinazolinyl group.
  • R 16 may be a substituent selected from the group consisting of Formulas 20 to 25:
  • M 1 to M 8 are each independently N or C (R 19 );
  • Any one of M 1 to M 4 bonded to L 6 in Formula 21 is C (R 19 ), wherein R 19 is absent;
  • K 2 and K 3 are each independently selected from the group consisting of a single bond, C (R 20 ) (R 21 ), N (R 22 ), O, S and SO 2 , but both K 2 and K 3 are a single bond Not;
  • Y 4 is selected from the group consisting of O, S, C (R 20 ) (R 21 ) and N (R 22 );
  • Z 3 to Z 6 are each independently N or C (R 19 );
  • n are each independently an integer from 0 to 4.
  • R 17 and R 18 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 Aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 An arylphosphanyl group, a C 6 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylamine group may be combined with or adjacent to a group to form a condensed ring,
  • R 19 to R 22 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine or adjacent groups bond to which they
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 17 to R 22 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • the compound represented by Formula 1 of the present invention can increase the binding force between the hole and the electron while having the bipolar (bipolar) characteristics of the entire molecule due to the various aromatic ring substituents connected to the basic skeleton. Therefore, when the compound is applied to the organic electroluminescent device, since it can exhibit excellent characteristics as a host material of the light emitting layer as compared to the conventional CBP, the phosphorescence properties of the device is improved, the hole injection ability and / or transport capacity, the luminous efficiency The driving voltage, lifespan characteristics and the like can be improved.
  • the energy level can be adjusted according to the substituents to have a wide bandgap (sky blue ⁇ red), and thus can be applied not only to the light emitting layer, but also to the electron transport auxiliary layer, electron transport layer, hole transport layer, hole injection layer, etc. Can be.
  • the glass transition temperature can be improved, thereby having a higher thermal stability than the conventional CBP.
  • the thermal stability of the compound may not only be improved, but also effective in suppressing crystallization of the organic layer including the compound of Formula 1. Therefore, the device including the compound of formula 1 according to the present invention can greatly improve the durability and life characteristics.
  • the electron transport auxiliary layer since the electron transport auxiliary layer has a high triplet energy, it may exhibit excellent efficiency due to the triplet-triplet fusion effect.
  • the exciton generated in the light emitting layer can be prevented from diffusing into the electron transporting layer or the hole transporting layer adjacent to the light emitting layer.
  • the number of excitons contributing to light emission in the light emitting layer may be improved, and thus the luminous efficiency of the device may be improved, and the durability and stability of the device may be improved, and thus the life of the device may be efficiently increased.
  • Most of the materials developed show physical characteristics that can be driven at low voltages, thereby improving their lifetime.
  • the compound of Formula 1 according to the present invention when adopted as a hole injection / transport layer material, an electron injection / transport layer material, a blue, green and / or red phosphorescent host material of an organic electroluminescent device, efficiency and lifespan compared to conventional CBP In terms of excellent effects can be achieved. Therefore, the compound according to the present invention can greatly contribute to improving the performance and lifespan of the organic EL device, and in particular, the device life improvement has a great effect in maximizing the performance in the full color organic light emitting panel.
  • R 16 may be a substituent selected from the group consisting of Formulas 26 to 29:
  • R 23 to R 25 are each independently hydrogen, deuterium, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ of C 40 cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 60 aryl group, C 5-60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6- C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ⁇ C 60 of the blood group and a C 6 ⁇ C 60 selected from the group consisting of an aryl amine
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl of the above R 23 to R 25 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • the R 23 to R 25 are each independently hydrogen, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group and a nuclear atoms of 5 to 60 heteroaryl group consisting of It may be selected from the group, more preferably, consisting of hydrogen, methyl, ethyl, propyl, butyl, phenyl, biphenyl, pyridinyl, pyrimidinyl, naphthalenyl, quinolinyl and quinazolinyl Can be selected from the group.
  • the substituent selected from the group consisting of Formula 20 to 25 may be a substituent selected from the group consisting of B-1 to B-22:
  • t is an integer from 0 to 5;
  • l and s are each independently an integer from 0 to 4.
  • v is an integer from 0 to 3;
  • u is an integer from 0 to 2;
  • R 26 and R 27 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or
  • alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group and aryl of the above R 26 and R 27 Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear
  • R 19 to R 22 are each as defined in Chemical Formulas 20 to 25.
  • two substituents adjacent to each other of the R 3 to R 7 are bonded to each other to form a C 4 ⁇ C 18 condensed aromatic ring or 4 to 14 condensed heteroaromatic ring of nuclear atoms Can be formed.
  • Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
  • the compound represented by Chemical Formula 1 may be synthesized according to a general synthetic method (Chem. Rev., 60: 313 (1960); J. Chem. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) et al. Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
  • organic electroluminescent device comprising the compound represented by the formula (1) according to the present invention.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer It includes a compound represented by the formula (1).
  • the compound may be used alone or mixed two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, a light emitting auxiliary layer, a life improvement layer, an electron transport layer, an electron transport auxiliary layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by 1.
  • the organic material layer including the compound represented by Chemical Formula 1 may be a light emitting layer.
  • the light emitting layer of the organic electroluminescent device may include a host material, and may include a compound represented by Chemical Formula 1 as the host material.
  • the compound represented by Chemical Formula 1 when included as a light emitting layer material of the organic electroluminescent device, preferably a green phosphorescent host, the binding force between the holes and the electrons in the light emitting layer is increased. Efficiency and power efficiency), lifespan, brightness and driving voltage can be improved.
  • the structure of the organic EL device according to the present invention described above is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron transport auxiliary layer may be further stacked between the emission layer and the electron transport layer, and an electron injection layer may be further stacked on the electron transport layer.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, the electron transport auxiliary layer and the electron injection layer may include a compound represented by the formula (1), preferably the light emitting layer is represented by the formula (1) It may include a compound represented.
  • the structure of the organic EL device according to the present invention may be a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, and an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device of the present invention may be formed using other materials and methods known in the art, except that at least one of the organic material layers (eg, the light emitting layer) is formed to include the compound represented by Chemical Formula 1. It may be prepared by forming an organic material layer and an electrode.
  • the organic material layer may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • A-1 (3.44 g, 10.0 mmol) under nitrogen stream, (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol), K 2 CO 3 (4.27 g, 30.0 mmol), Pd (PPh 3 ) 4 (0.58 g, 5 mol%) and X-Phos (0.8 g, 5.00 mmol) were added to 120 ml / 40 ml of THF / H 2 O and stirred at 90 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride and MgSO 4 was added and filtered. After removing the solvent of the filtered organic layer to obtain the target compound J-1 (3.08 g, yield 50%) using column chromatography.
  • A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4,6 instead of (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid Except for using -diphenyl-1,3,5-triazin-2-yl) boronic acid (2.77 g, 10.0 mmol) was subjected to the same process as in Synthesis Example 1 to J-5 (2.55) g, yield 47%).
  • A-2 (3.45 g, 10.0 mmol) was used instead of A-1 and (4- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid was used instead of (4- ( Except for using 4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid (3.53 g, 10.0 mmol) was carried out in the same manner as in Synthesis Example 1 J-6 (2.41 g, yield 39%) was obtained.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and 9,9 'was substituted for (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) boronic acid.
  • -J-16 (4.04 g, 49% yield) of the target compound by the same procedure as in Synthesis Example 1, except that spirobibi [fluorene] -4-ylboronic acid (3.60 g, 10.0 mmol) was used.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] furan-4-ylboronic acid (2.12 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-17 (3.24 g, yield 48%) was obtained.
  • A-6 (5.45 g, 10.0 mmol) was used instead of A-1 and (3- (4,6-diphenyl-1,3,5-triazin-2-yl) phenyl) dibenzo [b instead of boronic acid , d] thiophen-4-ylboronic acid (2.28 g, 10.0 mmol) was used in the same manner as in Synthesis Example 1, except that J-18 (3.25 g, yield 47%) was obtained. .
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / 90% of the host compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 (30) nm) / LiF (1 nm) / Al (200 nm) were laminated to fabricate an organic EL device.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound J-1 as the light emitting host material when the emission layer was formed.
  • Example 1-10 For each organic EL device produced in Example 1-10 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.
  • the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique comprenant celui-ci. Le composé selon la présente invention est utilisé sur une couche organique, de préférence une couche émettant de la lumière, d'un dispositif électroluminescent organique, ce qui permet d'améliorer l'efficacité d'émission de lumière, la tension de commande et la durée de vie dudit dispositif électroluminescent.
PCT/KR2016/014958 2015-12-22 2016-12-21 Composé organique et dispositif électroluminescent organique comprenant ledit composé Ceased WO2017111439A1 (fr)

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CN108822096A (zh) * 2018-04-27 2018-11-16 陕西莱特光电材料股份有限公司 一种新型主体发光材料及其合成方法与应用
WO2019039402A1 (fr) * 2017-08-23 2019-02-28 保土谷化学工業株式会社 Composé ayant une structure cyclique d'indéobenzoazole, et élément électroluminescent organique
WO2019181997A1 (fr) 2018-03-23 2019-09-26 保土谷化学工業株式会社 Composé comprenant une structure cyclique de benzimidazole et élément électroluminescent organique
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JPWO2019039402A1 (ja) * 2017-08-23 2020-07-30 保土谷化学工業株式会社 インデノベンゾアゾール環構造を有する化合物および有機エレクトロルミネッセンス素子
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CN113490730A (zh) * 2019-02-20 2021-10-08 罗门哈斯电子材料韩国有限公司 有机电致发光化合物以及包含其的有机电致发光装置
CN112521340A (zh) * 2020-11-23 2021-03-19 北京八亿时空液晶科技股份有限公司 一种有机电致发光材料及其应用
EP4206189A1 (fr) * 2021-12-30 2023-07-05 LG Display Co., Ltd. Composé organique et dispositif électroluminescent organique le comprenant
CN114656392A (zh) * 2022-03-30 2022-06-24 上海钥熠电子科技有限公司 有机化合物、有机光电器件及显示或照明装置
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